Phosphate → (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic Acid

HRID 382612ノート

反応式

HRID 382612 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:19]([O:21]CC3C=CC([N+]([O-])=O)=CC=3)=[O:20])=[C:8]([C:11]3[N:12]4[CH:18]=[N:17][CH:16]=[C:13]4[S:14][CH:15]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:19]([OH:21])=[O:20])=[C:8]([C:11]3[N:12]4[CH:18]=[N:17][CH:16]=[C:13]4[S:14][CH:15]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

5

反応物 2

HCID 1061PhosphateHCID 1317229014-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylate

生成物 1

HCID 20698522(1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic Acid収率 0.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4.70 g of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 10 ml of THF and 10 ml of {fraction (1/15)} M phosphate buffer was added 240 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 3 hours. The catalyst was collected by filtration and washed with water. The filtrate was washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 to give 27.5 mg of the title compound.

後処理

  1. customThe reactor was purged with hydrogen
  2. filtrationThe catalyst was collected by filtration
  3. washwashed with water
  4. washThe filtrate was washed with ethyl acetate
  5. customthe aqueous layer was purified by column chromatography on DIAION HP-20

出典と根拠

ORDレコード
ord-c3eb59ce70ca4e6690f321e5d6b3c451
出典データセット
uspto-grants-2001_10
特許番号
US06310056B1

反応ノート

読み込み中…